Compound and organic light emitting device using the same

ABSTRACT

Disclosed is an organic light emitting device. The organic light emitting device comprises a first electrode, organic material layer(s) comprising a light emitting layer, and a second electrode. The first electrode, the organic material layer(s), and the second electrode form layered structure and at least one layer of the organic material layer(s) include the compound of Formula 1 or the compound of Formula 1 into which a thermosetting or photo-crosslinkable functional group is introduced.

This application claims priority to International application No.PCT/KR2005/003179 filed on Sep. 23, 2005, and Korean Application No.10-2004-0077214 filed on Sep. 24, 2004, both of which are incorporatedby reference, as if fully set forth herein.

TECHNICAL FIELD

The present invention relates to an organic light emitting device whichcomprises a fluorene derivative capable of significantly improving alifespan, efficiency, and electrochemical and thermal stabilitiesthereof.

BACKGROUND ART

An organic light emission phenomenon is an example of a conversion ofcurrent into visible rays through an internal process of a specificorganic molecule. The organic light emission phenomenon is based on thefollowing mechanism. When organic material layers are interposed betweenan anode and a cathode, if voltage is applied between the twoelectrodes, electrons and holes are injected from the cathode and theanode into the organic material layer. The electrons and the holes whichare injected into the organic material layer are recombined to form anexciton, and the exciton is reduced to a bottom state to emit light. Anorganic light emitting device which is based on the above mechanismtypically comprises a cathode, an anode, and organic material layer(s),for example, organic material layers including a hole injection layer, ahole transport layer, a light emitting layer, and an electron transportlayer, interposed therebetween.

The materials used in the organic light emitting device are mostly pureorganic materials or complexes of organic material and metal. Thematerial used in the organic light emitting device may be classified asa hole injection material, a hole transport material, a light emittingmaterial, an electron transport material, or an electron injectionmaterial, according to its use. In connection with this, an organicmaterial having a p-type property, which is easily oxidized and iselectrochemically stable when it is oxidized, is mostly used as the holeinjection material or the hole transport material. Meanwhile, an organicmaterial having an n-type property, which is easily reduced and iselectrochemically stable when it is reduced, is used as the electroninjection material or the electron transport material. As the lightemitting layer material, an organic material having both p-type andn-type properties is preferable, which is stable when it is oxidized andwhen it is reduced. Also a material having high light emissionefficiency for conversion of the exciton into light when the exciton isformed is preferable.

In addition, it is preferable that the material used in the organiclight emitting device further have the following properties.

First, it is preferable that the material used in the organic lightemitting device have excellent thermal stability. The reason is thatjoule heat is generated by movement of electric charges in the organiclight emitting device. NPB, which has recently been used as the holetransport layer material, has a glass transition temperature of 100° C.or lower, thus it is difficult to apply to an organic light emittingdevice requiring a high current.

Second, in order to produce an organic light emitting device that iscapable of being actuated at low voltage and has high efficiency, holesand electrons which are injected into the organic light emitting devicemust be smoothly transported to a light emitting layer, and must not bereleased out of the light emitting layer. To achieve this, a materialused in the organic light emitting device must have a proper band gapand a proper HOMO or LUMO energy levels. A LUMO energy level ofPEDOT:PSS, which is currently used as a hole transport material of anorganic light emitting device produced using a solution coating method,is lower than that of an organic material used as a light emitting layermaterial, thus it is difficult to produce an organic light emittingdevice having high efficiency and a long lifespan.

Moreover, the material used in the organic light emitting device musthave excellent chemical stability, electric charge mobility, andinterfacial characteristic with an electrode or an adjacent layer. Thatis to say, the material used in the organic light emitting device mustbe little deformed by moisture or oxygen. Furthermore, proper hole orelectron mobility must be assured so as to balance densities of theholes and of the electrons in the light emitting layer of the organiclight emitting device to maximize the formation of excitons.Additionally, it has to be able to have a good interface with anelectrode including metal or metal oxides so as to assure stability ofthe device.

Accordingly, there is a need to develop an organic light emitting deviceincluding an organic material having the above-mentioned requirements inthe art.

DISCLOSURE OF INVENTION Technical Problem

Therefore, the object of the present inventions is to provide an organiclight emitting device which is capable of satisfying conditions requiredof a material usable for an organic light emitting device, for example,a proper energy level, electrochemical stability, and thermal stability,and which includes a fluorene derivative having a chemical structurecapable of playing various roles required in the organic light emittingdevice, depending on a substituent group.

Technical Solution

The present invention provides an organic light emitting device whichcomprises a first electrode, organic material layer(s) comprising alight emitting layer, and a second electrode, wherein the firstelectrode, the organic material layer(s), and the second electrode forma layered structure and at least one layer of the organic materiallayer(s) includes a compound of the following Formula 1 or a compound ofFormula 1 into which a thermosetting or photo-crosslinkable functionalgroup is introduced:

wherein X is C or Si;

A is

B is

a and b are zero or positive integer;

Y is a bond; bivalent aromatic hydrocarbons; bivalent aromatichydrocarbons which are substituted with at least one substituent groupselected from the group consisting of nitro, nitrile, halogen, alkyl,alkoxy, and amino groups; a bivalent heterocyclic group; or a bivalentheterocyclic group which is substituted with at least one substituentgroup selected from the group consisting of nitro, nitrile, halogen,alkyl, alkoxy, and amino groups.

Y1 to Y4 are each independently bivalent aromatic hydrocarbons; bivalentaromatic hydrocarbons which are substituted with at least onesubstituent group selected from the group consisting of nitro, nitrile,halogen, alkyl, alkoxy, and amino groups; a bivalent heterocyclic group;or a bivalent heterocyclic group which is substituted with at least onesubstituent group selected from the group consisting of nitro, nitrile,halogen, alkyl, alkoxy, and amino groups.

Z1 to Z8 are each independently hydrogen; aliphatic hydrocarbons havinga carbon number of 1-20; aromatic hydrocarbons; aromatic hydrocarbonswhich are substituted with at least one substituent group selected fromthe group consisting of the nitro, nitrile, halogen, alkyl, alkoxy,amino, aromatic hydrocarbon, and heterocyclic groups; a silicon groupsubstituted with aromatic hydrocarbons; a heterocyclic group; aheterocyclic group which is substituted with at least one substituentgroup selected from the group consisting of the nitro, nitrile, halogen,alkyl, alkoxy, amino, aromatic hydrocarbon, and heterocyclic groups; athiophene group which is substituted with hydrocarbons having a carbonnumber of 1-20 or aromatic hydrocarbons having a carbon number of 6-20;or a boron group which is substituted with aromatic hydrocarbons.

R1 to R4 and R6 to R9 are each independently selected from the groupconsisting of hydrogen, a substituted or unsubstituted alkyl group, asubstituted or unsubstituted alkoxy group, a substituted orunsubstituted alkenyl group, a substituted or unsubstituted aryl group,a substituted or unsubstituted arylamine group, a substituted orunsubstituted heterocyclic group, an amino group, a nitrile group, anitro group, a halogen group, an amide group, and an ester group. Theymay form aliphatic or hetero condensation rings along with adjacentgroups.

R5 is selected from the group consisting of hydrogen, a substituted orunsubstituted alkyl group, a substituted or unsubstituted cycloalkylgroup, a substituted or unsubstituted alkenyl group, a substituted orunsubstituted aryl group, and a substituted or unsubstitutedheterocyclic group.

Carbon at an ortho-position of the aryl or heterocyclic group and R4 orR6 may form a condensation ring along with a group selected from thegroup consisting of O, S, NR, PR, C═O, CRR′, and SiRR′, with the provisothat R5 is the aryl group or the heterocyclic group, wherein R and R′are each independently selected from the group consisting of hydrogen, asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedalkoxy group, a substituted or unsubstituted alkenyl group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylamine group, a substituted or unsubstituted heterocyclic group, anitrile group, an amide group, and an ester group, and R and R′ may forma condensation ring to form a spiro compound.

A detailed description will be given of the substituent groups ofFormula 1.

In Z1 to Z8 as the substituent groups of Formula 1, the aromaticcompounds are exemplified by monocyclic aromatic rings, such as phenyl,biphenyl, and terphenyl, and multicyclic aromatic rings, such asnaphthyl, anthracenyl, pyrenyl, and perylenyl. The hetero aromaticcompounds are exemplified by thiophene, furan, pyrrole, imidazole,thiazole, oxazole, oxadiazole, thiadiazole, triazole, pyridyl,pyridazyl, pyrazine, quinoline, and isoquinoline.

Examples of aliphatic hydrocarbons having a carbon number of 1-20include straight chain aliphatic hydrocarbons, branched chain aliphatichydrocarbons, saturated aliphatic hydrocarbons, and unsaturatedaliphatic hydrocarbons. They are exemplified by an alkyl group, such asa methyl group, an ethyl group, an n-propyl group, an isopropyl group,an n-butyl group, a sec-butyl group, an iso-butyl group, a ter-butylgroup, a pentyl group, and a hexyl group; an alkenyl group having adouble bond, such as styryl; and an alkynyl group having a triple bond,such as an acetylene group.

The carbon number of the alkyl, alkoxy, and alkenyl groups of R1 to R9of Formula 1 is not limited, but is preferably 1-20.

The length of the alkyl group contained in the compound does not affectthe conjugate length of the compound, but may affect the method ofapplying the compound to the organic light emitting device, for example,a vacuum deposition method or a solution coating method.

Illustrative, but non-limiting, examples of the aryl group of R1 to R9of Formula 1 include monocyclic aromatic rings, such as a phenyl group,a biphenyl group, a terphenyl group, and a stilbene group, andmulticyclic aromatic rings, such as a naphthyl group, an anthracenylgroup, a phenanthrene group, a pyrenyl group, and a perylenyl group.

Illustrative, but non-limiting, examples of the arylamine group of R1 toR9 of Formula 1 include a diphenylamine group, a dinaphthylamine group,a dibiphenylamine group, a phenylnaphthylamine group, aphenyldiphetylamine group, a ditolylamine group, a phenyltolylaminegroup, a carbazolyl group, and a triphenylamine group.

Illustrative, but non-limiting, examples of the heterocyclic group of R1to R9 of Formula 1 include a thiophene group, a furan group, a pyrrolylgroup, an imidazolyl group, a thiazolyl group, an oxazolyl group, anoxadiazolyl group, a triazolyl group, a pyridyl group, a pyradazinegroup, a quinolinyl group, an isoquinoline group, and an acridyl group.

In addition, illustrative, but non-limiting, examples of the alkenyl,aryl, arylamine, and heterocyclic groups of R1 to R9 of Formula 1include compounds shown in the following Formulae.

In the above Formulae, Z is a group selected from the group consistingof hydrogen, aliphatic hydrocarbons having a carbon number of 1-20, analkoxy group, an arylamine group, an aryl group, a heterocyclic group, anitrile group, and an acetylene group. Examples of the arylamine, aryl,and heterocyclic groups of Z are as shown in the above-mentionedsubstituent groups of R1 to R9.

According to a preferred embodiment of the present invention, R5 ofFormula 1 is an aryl or an heterocyclic group.

According to another preferred embodiment of the present invention, R5of Formula 1 is an aryl or an heterocyclic group, and carbon at anortho-position of the aryl or heterocyclic group and R4 or R6 form acondensation ring along with a group selected from the group consistingof O, S, NR, PR, C═O, CRR′, and SiRR′ (R and R′ are as defined inFormula 1).

According to still another preferred embodiment of the presentinvention, R5 of Formula 1 is an aryl or an heterocyclic group, andcarbon at the ortho-position of the aryl or heterocyclic group and R4,and carbon at the ortho-position of the aryl or heterocyclic group andR6 form the condensation ring along with a group selected from the groupconsisting of O, S, NR, PR, C═O, CRR′, and SiRR′ (R and R′ are asdefined in Formula 1).

According to the preferred embodiment of the present invention,illustrative, but non-limiting, examples of the compound of Formula 1include compounds of the following Formulae 2 to 119. [Formulae 2 to119]

In the above, Formulae, A and B are as defined in Formula 1.

Illustrative, but non-limiting, examples of A and B are as follows.Combination of the compounds of Formulae 2 to 119 and the followingsubstituent groups A and B can form various derivative compounds. Forexample, if the compound of Formula 2 is combined with the substituentgroup 1, the resulting product will be designated by the compound ofFormula 2-1.

[A and B]

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 illustrates an organic light emitting device comprising asubstrate 1, an anode 2, a light emitting layer 3, and a cathode 4; and

FIG. 2 illustrates an organic light emitting device comprising asubstrate 1, an anode 2, a hole injection layer 5, a hole transportlayer 6, a light emitting layer 7, an electron transport layer 8, and acathode 4.

BEST MODE FOR CARRYING OUT THE INVENTION

Hereinafter, a detailed description will be given of the presentinvention.

Various substituent groups are introduced into a core structure shown inFormula 1, in detail, the core structure in which a fluorene group isbonded to a combination of an acridine group and a carbazolyl group toform a spiro structure, thereby the compound of Formula 1 hascharacteristics suitable for application to an organic material layerused in an organic light emitting device. This will be described indetail, below.

The steric core structure of the compound of Formula 1 can be dividedinto two portions, A and B, for explanation as shown in the followingFormula.

The compound of Formula 1 has the steric core structure in which a planeA meets with a plane B at right angles around X, and conjugation doesnot occur between the A and B portions around X. Furthermore, since onenitrogen atom is positioned among three aryl groups in the plane B,conjugation is limited in the plane B.

The conjugation length of the compound has a close relationship with anenergy band gap. In detail, the energy band gap is reduced as theconjugation length of the compound increases. As described above, sincea conjugation structure is limited in the core structure of the compoundof Formula 1, the core structure has a large energy band gap.

As described above, in the present invention, various substituent groupsare introduced to R1 to R9 positions and Z1 to Z8 positions of the corestructure having the large energy band gap so as to produce compoundshaving various energy band gaps. Generally, it is easy to control theenergy band gap by introducing substituent groups into a core structurehaving a large energy band gap, but it is difficult to significantlycontrol the energy band gap by introducing substituent groups into acore structure having a small energy band gap. Furthermore, in thepresent invention, it is possible to control HOMO and LUMO energy levelsof the compound by introducing various substituent groups into R1 to R9and Z1 to Z8 of the core structure.

Additionally, various substituent groups are introduced into the corestructure to produce compounds having intrinsic characteristics of thesubstituent groups. For example, substituent groups, which arefrequently applied to hole injection layer, hole transport layer, lightemitting layer, and electron transport layer materials during theproduction of the organic light emitting device, are introduced into thecore structure so as to produce substances capable of satisfying therequirements of each organic material layer. Particularly, since thecore structure of the compound of Formula includes the arylaminestructure, it has an energy level suitable for the hole injection and/orhole transport materials in the organic light emitting device. In thepresent invention, the compound having the proper energy level isselected depending on the substituent group among the compoundsrepresented by Formula 1 to be used in the organic light emittingdevice, thereby it is possible to realize a device having a lowactuating voltage and a high light efficiency.

Furthermore, various substituent groups are symmetrically introducedinto the core structure (the A and B portions are located at both sidesof the core structure) so as to precisely control the energy band gap,improve interfacial characteristics with organic materials, and applythe compound to various fields.

As well, if the numbers of nitrogen contained in the substituent groupsA and B are each set to 2 or more (if Y1 to Y4 and Z1 to Z8 are heteroaromatic amine compounds, the number of nitrogen contained in them isnot counted), it is possible to precisely control the HOMO and LUMOenergy levels and the energy band gap, and on the other hand interfacialcharacteristics with the organic materials is improved and thereby makeit possible to apply the compound to various fields.

Additionally, various substituent groups are introduced into the stericstructure of the compound of Formula 1 using spiro bonding to controlthe three-dimensional structure of the organic material so as tominimize π-π interaction in the organic material, thereby formation ofexcimers is prevented.

Meanwhile, since the compound of Formula 1 has a high glass transitiontemperature (Tg), it has excellent thermal stability. For example, theglass transition temperature of the compound of Formula 3-1 is 159° C.,which is still higher than that of conventionally used NPB (Tg: 96° C.).Such increase in thermal stability is an important factor providingactuating stability to the device.

Furthermore, the compound of Formula 1 may be used to form the organicmaterial layer using a vacuum deposition process or a solution coatingprocess during the production of the organic light emitting device. Inconnection with this, illustrative, but non-limiting, examples of thesolution coating process include a spin coating process, a dip coatingprocess, an inkjet printing process, a screen printing process, a sprayprocess, and a roll coating process.

For example, the compound of Formula 1 has excellent solubility to apolar solvent, such as xylene, dichloroethane, or NMP, which is usedduring the production of the device, and forms a thin film very wellthrough the process using a solution, thus the solution coating processmay be applied to produce the device.

Tertiary alcohol, which is produced by a reaction of a lithiated aryland keto group, is heated in the presence of an acid catalyst to form ahexagonal cyclic structure while water is removed, thereby producing thecompound having a spiro structure according to the present invention.The above-mentioned procedure for producing the compound is well knownin the art, and those skilled in the art can change the productionconditions during the production of the compound of Formula 1. Theproduction will be described in detail in the preparation exampleslater.

In the organic light emitting device of the present invention, acompound, in which a thermosetting or photo-crosslinkable functionalgroup is introduced into the compound of Formula 1, may be used insteadof the compound of Formula 1. The former compound has the basic physicalproperties of the compound of Formula 1, and may be used to form a thinfilm using a solution coating process and then be cured so as to form anorganic material layer during the production of the device.

The method of forming the organic material layer, which comprisesintroducing the curable functional group into the organic materialduring the production of the organic light emitting device, forming theorganic thin film using the solution coating process, and curing theresulting film, is disclosed in U.S. Pat. No. 2003-0044518 and EP Pat.No. 1146574A2.

The above documents state that, if the organic material layer is formedthrough the above-mentioned method using a material having athermosetting or photo-crosslinkable vinyl or acryl group so as toproduce an organic light emitting device, it is possible to produce anorganic light emitting device having a low voltage and high brightnessas well as an organic light emitting device having a multilayeredstructure using the solution coating process. This operation mechanismmay be applied to the compound of the present invention.

In the present invention, the thermosetting or photo-crosslinkablefunctional group may be a vinyl or acryl group.

The organic light emitting device of the present invention can beproduced using known materials through a known process, modified only inthat at least one layer of organic material layer(s) include thecompound of the present invention, that is, the compound of Formula 1.

The organic material layer(s) of the organic light emitting deviceaccording to the present invention may have a single layer structure, oralternatively, a multilayered structure in which two or more organicmaterial layers are layered. For example, the organic light emittingdevice of the present invention may comprise a hole injection layer, ahole transport layer, a light emitting layer, an electron transportlayer, or an electron injection layer as the organic material layer(s).However, the structure of the organic light emitting device is notlimited to this, but may comprise a smaller number of organic materiallayers.

Furthermore, the organic light emitting device of the present inventionmay be produced, for example, by sequentially layering a firstelectrode, organic material layer(s), and a second electrode on asubstrate. In connection with this, a physical vapor deposition (PVD)method, such as a sputtering method or an e-beam evaporation method, maybe used, but the method is not limited to these.

A method of producing the compound of Formula 1 and the production ofthe organic light emitting device using the same will be described indetail in the following preparation examples and examples. However, thefollowing preparation examples and examples are set forth to illustrate,but are not to be construed to limit the present invention.

MODE FOR THE INVENTION

A better understanding of a method of producing an organic compoundrepresented by Formula 1 and the production of an organic light emittingdevice using the same may be obtained in light of the followingpreparation examples and examples which are set forth to illustrate, butare not to be construed to limit the present invention.

In order to produce the compound represented by Formula 1, compounds ofthe following Formulae, a or b, may be used as a starting material.

PREPARATION EXAMPLE 1 Production of a Starting Material Represented byFormula a

1) After 10 g of diphenylamine (59 mmol) and 8.04 ml of bromomethylmethyl ether (88.6 mmol) were dissolved in 100 ml of tetrahydrofuran,12.4 ml of triethylamine (88.6 mmol) were added thereto. Stirring wasconducted in a nitrogen atmosphere for 5 hours, and an organic layer wasthen extracted using distilled water. The extracted organic layer wassubjected to a column separation process at a ratio ofn-hexane/tetrahydrofuran of 15:1, and vacuum dried to produce 12 g oftertiary amine (yield 90%).

2) The amine compound produced in 1) (12.0 g, 56.3 mmol) was dissolvedin 100 ml of purified THF and cooled to −78° C., and n-BuLi (2.5 Mhexane solution, 22.5 ml, 56.3 mmol) was slowly dropped thereon.Stirring was conducted at the same temperature for 30 min, and a2,7-dichloro-9-fluorenone compound (14.0 g, 56.3 mmol) was addedthereto. After stirring at the same temperature for 40 min, thetemperature was raised to normal temperature and stirring was carriedout for an additional 3 hours. The reaction was completed in an ammoniumchloride aqueous solution, and extraction was conducted with ethylether. Water was removed from an organic material layer using anhydrousmagnesium sulfate, and an organic solvent was then removed therefrom.The produced solid was dispersed in ethanol, stirred for one day,filtered, and vacuum dried. After an intermediate material was dispersedin 100 ml of acetic acid, ten drops of concentrated sulfuric acid wereadded thereto and reflux was conducted for 4 hours. The resulting solidwas filtered, washed with ethanol, and vacuum dried to produce 21.8 g ofamine (96.8% yield). MS: [M+H]+=401.

PREPARATION EXAMPLE 2 Preparation of a Starting Material Represented byFormula b

A compound of Formula a (9.00 g, 22.5 mmol), 1-iodonaphthalene (11.4 g,45.0 mmol), potassium carbonate (6.22 g, 45.0 mmol), copper iodide (214mg, 1.13 mmol), and xylene (250 ml) were heated in a nitrogen atmosphereovernight. After cooling to normal temperature, a product was extractedwith ethyl acetate, water was removed with anhydrous magnesium sulfate,and the solvent was removed at a reduced pressure. The resulting productwas passed through a silica gel column using a hexane solvent to producea compound, the solvent was removed at a reduced pressure, and vacuumdrying was conducted to produce the compound of Formula b (5.0 g, 42%yield). MS: [M+H]⁺=527.

EXAMPLE 1 Preparation of the Compound Represented by Formula 3-1

1) Synthesis of arylamine(4-(N-phenyl-N-phenylamino)phenyl-1-phenylamine) to produce the compoundrepresented by Formula 3-1:13.5 g of4-bromophenyl-N-phenyl-N-phenylamine (41.6 mmol) and 3.98 ml of aniline(43.7 mmol) were dissolved in 120 ml of toluene, 10.00 g ofsodium-tert-butoxide (104.1 mmol), 0.48 g of bis(dibenzylideneacetone)palladium(0) (0.83 mmol), and 0.58 ml of 50 wt %tri-tert-butylphosphine toluene solution (1.25 mmol) were added thereto,and reflux was conducted in a nitrogen atmosphere for 2 hours. Distilledwater was added to the reaction solution to complete the reaction, andthe organic layer was extracted. A column separation process wasconducted using a solvent of n-hexane and tetrahydrofuran at a ratio of10:1, stirring was conducted using petroleum ether, and vacuum dryingwas conducted to produce an arylamine connection group (9.6 g, yield69%). MS: [M+H]⁺=336.

2) 4.68 g of compound of Formula b (8.88 mmol) and 6.86 g of4-(N-phenyl-N-phenylamino)phenyl-1-phenylamine (20.4 mmol) weredissolved in 120 ml of toluene, 5.89 g of sodium-tert-butoxide (61.3mmol), 0.24 g of tris(dibenzylidene acetone)dipalladium(0) (0.41 mmol),and 0.25 ml of 50 wt % tri-tert-butylphosphine toluene solution (0.61mmol) were added thereto, and reflux was conducted in a nitrogenatmosphere for 2 hours. Distilled water was added to the reactionsolution to complete the reaction, and the organic layer was extracted.A column separation process was conducted using a solvent of n-hexaneand tetrahydrofuran at a ratio of 4:1, stirring was conducted usingpetroleum ether, and vacuum drying was conducted to produce the compoundof Formula 3-1 (5.2 g, yield 52%). MS: [M+H]⁺=1127.

EXAMPLE 2 Preparation of the Compound Represented by Formula 3-2

1) Synthesis of arylamine(4-(N-phenyl-N-phenylamino)phenyl-1-naphthylamine) to produce thecompound represented by Formula 3-2:15.0 g of4-bromophenyl-N-phenyl-N-phenylamine (46.3 mmol) and 7.29 g of1-naphthylamine (50.9 mmol) were dissolved in 200 ml of toluene, 13.34 gof sodium-tert-butoxide (138.8 mmol), 0.53 g of bis(dibenzylideneacetone)palladium(0) (0.93 mmol), and 0.56 ml of 50 wt %tri-tert-butylphosphine toluene solution (1.39 mmol) were added thereto,and reflux was conducted in a nitrogen atmosphere for 2 hours. Distilledwater was added to the reaction solution to complete the reaction, andthe organic layer was extracted. A column separation process wasconducted using a solvent of n-hexane and tetrahydrofuran at a ratio of10:1, stirring was conducted using petroleum ether, and vacuum dryingwas conducted to produce an arylamine connection group (13 g, yield73%). MS: [M+H]⁺=386.

2) 4.68 g of compound of Formula b (8.88 mmol) and 7.88 g of4-(N-phenyl-N-phenylamino)phenyl-1-naphthylamine (20.4 mmol) weredissolved in 120 ml of toluene, 5.89 g of sodium-tert-butoxide (61.3mmol), 0.24 g of tris(dibenzylidene acetone)dipalladium(0) (0.41 mmol),and 0.25 ml of 50 wt % tri-tert-butylphosphine toluene solution (0.61mmol) were added thereto, and reflux was conducted in a nitrogenatmosphere for 2 hours. Distilled water was added to the reactionsolution to complete the reaction, and the organic layer was extracted.A column separation process was conducted using a solvent of n-hexaneand tetrahydrofuran at a ratio of 4:1, stirring was conducted usingpetroleum ether, and vacuum drying was conducted to produce the compoundof Formula 3-2 (5.4 g, yield 50%). MS: [M+H]⁺=1227.

EXAMPLE 3 Preparation of the Compound Represented by Formula 3-4

1) Synthesis of arylamine(4-(N-phenyl-N-phenylamino)phenyl-1-biphenylamine) to produce thecompound represented by Formula 3-4:17.4 g of4-bromophenyl-N-phenyl-N-phenylamine (53.7 mmol) and 9.99 g of4-aminobiphenyl (59.0 mmol) were dissolved in 250 ml of toluene, 17.02 gof sodium-tert-butoxide (177.1 mmol), 0.68 g of bis(dibenzylideneacetone)palladium(0) (1.2 mmol), and 0.72 ml of 50 wt %tri-tert-butylphosphine toluene solution (1.8 mmol) were added thereto,and reflux was conducted in a nitrogen atmosphere for 2 hours. Distilledwater was added to the reaction solution to complete the reaction, andthe organic layer was extracted. A column separation process wasconducted using a solvent of n-hexane and tetrahydrofuran at a ratio of10:1, stirring was conducted using petroleum ether, and vacuum dryingwas conducted to produce an arylamine connection group (16 g, yield73%). MS: [M+H]⁺=412.

2) 4.68 g of compound of Formula b (8.88 mmol) and 8.42 g of4-(N,N-diphenylamino)phenyl-4-biphenylamine (20.4 mmol) were dissolvedin 120 ml of toluene, 5.89 g of sodium-tert-butoxide (61.3 mmol), 0.24 gof tris(dibenzylidene acetone)dipalladium(0) (0.41 mmol), and 0.25 ml of50 wt % tri-tert-butylphosphine toluene solution (0.61 mmol) were addedthereto, and reflux was conducted in a nitrogen atmosphere for 2 hours.Distilled water was added to the reaction solution to complete thereaction, and the organic layer was extracted. A column separationprocess was conducted using a solvent of n-hexane and tetrahydrofuran ata ratio of 4:1, stirring was conducted using petroleum ether, and vacuumdrying was conducted to produce the compound of Formula 3-4 (5.2 g,yield 45.8%). MS: [M+H]⁺=1279.

EXAMPLE 4 Preparation of the Compound Represented by Formula 3-21

1) Synthesis of arylamine(4-(N-phenyl-N-naphthylamino)phenyl-1-biphenylamine) to produce thecompound represented by Formula 3-21:14.0 g of4-bromophenyl-N-phenyl-N-naphthylamine (37.4 mmol) and 6.96 g of4-aminobiphenyl (41.2 mmol) were dissolved in 200 ml of toluene, 0.47 gof bis(dibenzylidene acetone)palladium(0) (0.82 mmol), 0.50 ml of 50 wt% tri-tert-butylphosphine toluene solution (1.2 mmol), and 11.86 g ofsodium-tert-butoxide (123.4 mmol) were added thereto. After reflux wasconducted in a nitrogen atmosphere for 2 hours, distilled water wasadded to the reaction solution to complete the reaction. The organiclayer was extracted, and a column separation process was conducted usinga developing solvent of n-hexane and tetrahydrofuran at a ratio of 10:1,stirring was conducted using petroleum ether, and vacuum drying wasconducted to produce an arylamine connection group (7.5 g, yield 43%).MS: [M+H]⁺=462.

2) 4.68 g of compound of Formula b (8.88 mmol) and 9.44 g of4-(N-phenyl-1-naphthylamino)phenyl-4-biphenylamine (20.4 mmol) weredissolved in 120 ml of toluene, 5.89 g of sodium-tert-butoxide (61.3mmol), 0.24 g of tris(dibenzylidene acetone)dipalladium(0) (0.41 mmol),and 0.25 ml of 50 wt % tri-tert-butylphosphine toluene solution (0.61mmol) were added thereto, and reflux was conducted in a nitrogenatmosphere for 2 hours. Distilled water was added to the reactionsolution to complete the reaction, and the organic layer was extracted.A column separation process was conducted using a solvent of n-hexaneand tetrahydrofuran at a ratio of 4:1, stirring was conducted usingpetroleum ether, and vacuum drying was conducted to produce the compoundof Formula 3-21 (5.5 g, yield 45%). MS: [M+H]⁺=1379.

EXAMPLE 5 Production of an Organic Light Emitting Device

A glass substrate (corning 7059 glass), on which ITO (indium tin oxide)was applied to a thickness of 1000 Å to form a thin film, was put indistilled water, in which a detergent was dissolved, and washed usingultrasonic waves. In connection with this, a product manufactured byFischer Inc. was used as the detergent, and distilled water was producedby filtering twice using a filter manufactured by Millipore Inc. AfterITO was washed for 30 min, ultrasonic washing was conducted twice usingdistilled water for 10 min. After the washing using distilled water wascompleted, ultrasonic washing was conducted using isopropyl alcohol,acetone, and methanol solvents, and drying was then conducted. Next, itwas transported to a plasma washing machine. The substrate was drywashed using oxygen plasma for 5 min, and then transported to a vacuumevaporator.

Hexanitrile hexaazatriphenylene (hereinafter, referred to as “HAT”) ofthe following Formula was vacuum deposited to a thickness of 80 Å byheating on a transparent ITO electrode, which was prepared through theabove procedure, so as to form an anode including an ITO conductivelayer and an N-type organic material.

Interfacial characteristics between the substrate and a hole injectionlayer can be improved using the thin film. Subsequently, the compound ofFormula 3-1 was deposited to a thickness of 800 Å on the thin film toform the hole injection layer. NPB was deposited thereon to a thicknessof 300 Å so as to form a hole transport layer, and Alq3 was depositedthereon to a thickness of 300 Å to form the light emitting layer. Anelectron transport layer material of the following Formula was depositedto a thickness of 200 Å on the light emitting layer to form an electrontransport layer.

Lithium fluoride (LiF) having a thickness of 12 Å and aluminum having athickness of 2000 Å were sequentially deposited on the electrontransport layer to form a cathode.

In the above procedure, the deposition speed of an organic material wasmaintained at 0.3-0.8 Å/sec. Furthermore, lithium fluoride and aluminumwere deposited at speeds of 0.3 Å/sec and 1.5-2.5 Å/sec, respectively,on the cathode. During the deposition, a vacuum was maintained at1−3×10⁻⁷.

The resulting device had an electric field of 4.76 V at a forwardcurrent density of 100 mA/cm², and a spectrum having a light efficiencyof 1.93 lm/W. The operation and light emission of the device at theabove-mentioned actuating voltage mean that the compound of Formula 3-1,which formed the layer between the thin film on the substrate and thehole transport layer, functions to inject holes.

EXAMPLE 6 Production of an Organic Light Emitting Device

The procedure of example 5 was repeated to produce a device except thatthe compound of Formula 3-1 used as a hole injection layer wassubstituted with the compound of Formula 3-2.

The resulting device had an electric field of 4.72 V at a forwardcurrent density of 100 mA/cm², and a spectrum having a light efficiencyof 1.94 lm/W. The operation and light emission of the device at theabove-mentioned actuating voltage mean that the compound of Formula 3-2,which formed a layer between a thin film on a substrate and a holetransport layer, functions to inject holes.

EXAMPLE 7 Production of an Organic Light Emitting Device

The procedure of example 5 was repeated to produce a device except thatthe compound of Formula 3-1 used as a hole injection layer wassubstituted with the compound of Formula 3-4.

The resulting device had an electric field of 4.65 V at a forwardcurrent density of 100 mA/cm², and a spectrum having a light efficiencyof 1.92 lm/W. The operation and light emission of the device at theabove-mentioned actuating voltage mean that the compound of Formula 3-4,which formed a layer between a thin film on a substrate and a holetransport layer, functions to inject holes.

EXAMPLE 8 Production of an Organic Light Emitting Device

The procedure of example 5 was repeated to produce a device except thatthe compound of Formula 3-1 used as a hole injection layer wassubstituted with the compound of Formula 3-21.

The resulting device had an electric field of 4.60 V at a forwardcurrent density of 100 mA/cm², and a spectrum having a light efficiencyof 1.97 lm/W. The operation and light emission of the device at theabove-mentioned actuating voltage mean that the compound of Formula3-21, which formed a layer between a thin film on a substrate and a holetransport layer, functions to inject holes.

INDUSTRIAL APPLICABILITY

The compound of the present invention can be used as an organic materiallayer material, particularly, hole injection and/or transport materialsin an organic light emitting device, and when applied to an organiclight emitting device it is possible to reduce the actuating voltage ofthe device, to improve the light efficiency thereof, and to improve thelifespan of the device through the thermal stability of the compound.

1. An organic light emitting device, comprising: a first electrode;organic material layer(s) comprising a light emitting layer, wherein atleast one layer of the organic material layer(s) includes the compoundof Formula 1; and a second electrode; wherein the first electrode, theorganic material layer(s), and the second electrode form a layeredstructure,

wherein X is C or Si;

A is

B is a and b are zero or positive integer; Y is a bond; bivalentaromatic hydrocarbons; bivalent aromatic hydrocarbons which aresubstituted with at least one substituent group selected from the groupconsisting of nitro, nitrile, halogen, alkyl, alkoxy, and amino groups;a bivalent heterocyclic group; or a bivalent heterocyclic group which issubstituted with at least one substituent group selected from the groupconsisting of nitro, nitrile, halogen, alkyl, alkoxy, and amino groups;Y1 to Y4 are each independently bivalent aromatic hydrocarbons; bivalentaromatic hydrocarbons which are substituted with at least onesubstituent group selected from the group consisting of nitro, nitrile,halogen, alkyl, alkoxy, and amino groups; a bivalent heterocyclic group;or a bivalent heterocyclic group which is substituted with at least onesubstituent group selected from the group consisting of nitro, nitrile,halogen, alkyl, alkoxy, and amino groups; Z1 to Z8 are eachindependently hydrogen; aliphatic hydrocarbons having a carbon number of1-20; aromatic hydrocarbons; aromatic hydrocarbons which are substitutedwith at least one substituent group selected from the group consistingof the nitro, nitrile, halogen, alkyl, alkoxy, amino, aromatichydrocarbon, and heterocyclic groups; a silicon group substituted witharomatic hydrocarbons; a heterocyclic group; a heterocyclic group whichis substituted with at least one substituent group selected from thegroup consisting of the nitro, nitrile, halogen, alkyl, alkoxy, amino,aromatic hydrocarbon, and heterocyclic groups; a thiophene group whichis substituted with hydrocarbons having a carbon number of 1-20 oraromatic hydrocarbons having a carbon number of 6-20; or a boron groupwhich is substituted with aromatic hydrocarbons; R1 to R4, and R6 to R9are each independently selected from the group consisting of hydrogen, asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedalkoxy group, a substituted or unsubstituted alkenyl group, asubstituted or unsubstituted aryl group, a substituted or unsubstitutedarylamine group, a substituted or unsubstituted heterocyclic group, anamino group, a nitrile group, a nitro group, a halogen group, an amidegroup, and an ester group, and R1 to R4 and R6 to R9 may form aliphaticor hetero condensation rings along with adjacent groups; R5 is selectedfrom the group consisting of hydrogen, a substituted or unsubstitutedalkyl group, a substituted or unsubstituted cycloalkyl group, asubstituted or unsubstituted alkenyl group, a substituted orunsubstituted aryl group, and a substituted or unsubstitutedheterocyclic group; and with a proviso that when R5 is the aryl group orthe heterocyclic group, carbon at an ortho-position of the aryl orheterocyclic group and R4 or R6 may form a condensation ring along witha group selected from the group consisting of O, S, NR, PR, C═O, CRR′,and SiRR', wherein R and R′ each independently are selected from thegroup consisting of hydrogen, a substituted or unsubstituted alkylgroup, a substituted or unsubstituted alkoxy group, a substituted orunsubstituted alkenyl group, a substituted or unsubstituted aryl group,a substituted or unsubstituted arylamine group, a substituted orunsubstituted heterocyclic group, a nitrile group, an amide group, andan ester group, and may form a condensation ring to form a spirocompound.
 2. The organic light emitting device as set forth in claim 1,wherein R5 of Formula 1 is an aryl or a heterocyclic group.
 3. Theorganic light emitting device as set forth in claim 2, wherein R5 ofFormula 1 is an aryl or a heterocyclic group, and carbon at theortho-position of the aryl or heterocyclic group and R4 or R6 form thecondensation ring along with a group selected from the group consistingof O, S, NR, PR, C═O, CRR′, and SiRR′.
 4. The organic light emittingdevice as set forth in claim 1, wherein the compound of Formula 1 is anyone of compounds of Formulae 2 to 119: [Formulae 2 to 119]


5. The organic light emitting device as set forth in claim 4, wherein Aand B are each independently any one of following groups:


6. The organic light emitting device as set forth in claim 1, whereinthe organic material layer(s) comprise a hole transport layer, and thehole transport layer includes the compound of Formula
 1. 7. The organiclight emitting device as set forth in claim 1, wherein the organicmaterial layer(s) comprise a hole injection layer, and the holeinjection layer includes the compound of Formula
 1. 8. The organic lightemitting device as set forth in claim 1, wherein the organic materiallayer(s) comprise a layer which both injects and transports holes andwhich includes the compound of Formula 1.